A rural landscape with snow-covered fields, a winding road, and scattered trees.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Hillsdale vacation homes

Exterior

1. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ￥46,016
￥85,897 total
includes taxes & fees
Aug 9 - Aug 10
Gorgeous Mountain Views Retreat: Family & Nature
TV, fireplace, printers

2. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥89,529
￥209,713 total
includes taxes & fees
Aug 6 - Aug 7
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

3. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥36,045
￥54,856 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Riverside Berkshires Retreat
3 bedrooms, iron/ironing board, WiFi, bed sheets

4. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥68,749
￥111,938 total
includes taxes & fees
Sep 1 - Sep 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
TV, fireplace, stereo

5. Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (51 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
Great Barrington, Cabin Sleeps 14, Walk To Town
Coffee/tea maker, fridge, microwave, oven

6. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,476
￥64,315 total
includes taxes & fees
Aug 12 - Aug 13
Home in Great Barrington
Property grounds

7. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥39,330
￥63,608 total
includes taxes & fees
Aug 9 - Aug 10
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Pool

8. Charming Hudson Valley Escape | Heated Pool & Fire Pit

Charming Hudson Valley Escape | Heated Pool & Fire Pit
Claverack-Red Mills
10.0 out of 10, Exceptional, (1 review)
"amazing property - best rental i’ve ever stayed at. can’t recommend it enough"
United States
jessica c.
The price is ￥83,753
￥149,660 total
includes taxes & fees
Aug 12 - Aug 13
Charming Hudson Valley Escape | Heated Pool & Fire Pit
Exterior detail

9. Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ￥57,107
￥101,863 total
includes taxes & fees
Aug 23 - Aug 24
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Outdoor dining

10. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
Stockbridge In-town Escape
Smart TV

11. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is ￥37,285
￥75,739 total
includes taxes & fees
Aug 19 - Aug 20
stylish Berkshires Retreat
Terrace/patio

12. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
Athens
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful property that was clean. Hosts left information about surrounding area and restaurants- we definitely felt welcomed when we arrived. Beautiful area with lots to do! Would stay here again"
United States
Sarah M.
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Interior

13. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ￥47,039
￥58,851 total
includes taxes & fees
Aug 30 - Aug 31
rural, serene + sophisticated space
Outdoor dining

14. Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
10.0 out of 10, Exceptional, (1 review)
"We were only there for one night, but we really liked this space - it was clean and the beds were so comfortable! Thanks so much to our host for opening his home to us."
United States
Rachel P.
The price is ￥33,841
￥54,649 total
includes taxes & fees
Aug 5 - Aug 6
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
TV

15. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥51,916
￥100,770 total
includes taxes & fees
Sep 2 - Sep 3
Treetop Hideaway in Tyringham
Exterior detail

16. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is ￥52,388
￥111,534 total
includes taxes & fees
Aug 25 - Aug 26
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
TV, fireplace, books

17. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥45,513
￥126,012 total
includes taxes & fees
Aug 17 - Aug 18
NEW: Chic Modern Barn Style Home in Fun Area
Coffee/tea maker, fridge, microwave, oven

18. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (14 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is ￥140,015
￥228,512 total
includes taxes & fees
Aug 11 - Aug 12
A Country Lodge Straight Out of the Pages of a Great Novel
Coffee/tea maker, fridge, microwave, oven

19. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is ￥69,221
￥128,096 total
includes taxes & fees
Sep 2 - Sep 3
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Property grounds

20. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,707
￥22,237 total
includes taxes & fees
Aug 5 - Aug 6
All the comforts of home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"We had an easy time finding it,close to shopping. Would stay again"
LYNN 1-night trip
Posted 19 hours ago
Quality Inn Lee - Lenox South

Find out more about Hillsdale

Hillsdale Vacation Homes information

Number of reviews
281
Accommodation
668 Vacation Homes
Lowest Price
￥22,237
Highest Price
￥228,512